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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl tetramethylene bis-carbamate derivatives and per-ethylated pillar[5]arene Shuhan Xiong, Xiaoning Zhang, Lu-Bo Meng, Juli Jiang, Chen Lin,* Leyong Wang State Key Laboratory of Coordination Chemistry, Center for Multimolecular rganic Chemistry, School of Chemistry and Chemical Engineering, anjing University, anjing , China. Fax: ; Tel: ; Table of Contents 1. Materials and methods...s2 2. Synthesis of Guest...S3 3. Investigation of the interactions between EtP[5]A and Guest by 1 MR...S15 4. Partial 2D SEY MR spectra of G1 EtP[5]A...S18 5. Study of the photocleavage G7 EtP[5]A via UV 365nm by 1 MR...S19 6. Reference...S19 1. Materials and methods S1
2 All reactions were performed in atmosphere unless noted. All reagents were commercially available and use as supplied without further purification. Solvents were either employed as purchased or dried according ti procedures described in the literature. Compound EtP[5]A was prepared by published literature procedures. S1 MR spectra were collected on either a Bruker Avance DMX 300 Mz spectrometer or a Bruker Avance DMX 400 Mz spectrometer with internal standard tetramethylsilane (TMS) and signals as internal references, and the chemical shifts (δ) were expressed in ppm. 2D CSY and ESY experiments were performed on a Bruker DPX 400 Mz spectrometer. Low-resolution electrospray ionization mass spectra (LR- ESI-MS) were obtained on Finnigan MatTSQ 7000 instruments. igh-resolution electrospray ionization mass spectra (R-ESI-MS) were recorded on an Agilent 6540Q-TF LCMS equipped with an electrospray ionization (ESI) probe operating in positive-ion mode with direct infusion. 2. Synthesis of Guest S2
3 Cl Et 3 DCM Scheme S1 Synthesis of G1 Synthesis of G1: 1,4-butanediamine (0.44 g, 5 mmol) and triethylamine (1.02 g, 10 mmol) were added in dichloromethane (50 ml). Then benzyl chloroformate (1.71 g, 10 mmol) was dropped to the mixture in ice-bath in 10 minutes. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered and washed with dichloromethane. The filtrate was washed by brine and dried by a 2 S 4. The organic layer was evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 160/1, v/v) to afford G1 (1.64 g, 92.0 %), m.p C. 1 MR (300 Mz, chloroform-d, 298 K) δ (ppm): (m, 10, Ar), 5.10 (s, 4, C 2 ), 4.79 (s, 2, ), 3.20 (s, 4, C 2 ), 1.53 (s, 4, C 2 ). 13 C MR (75 Mz, chloroform-d, 298 K) δ (ppm): 156.5, 136.6, 128.5, 128.1, 66.7, 40.6, LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd for [M + a] +, , found R-ESI-MS is: m/z calcd for [M + a] +, C a +, , found Fig. S1 1 MR spectrum (300 Mz, chloroform-d, 298 K) of G1 S3
4 Fig. S2 13 C MR spectrum (75 Mz, chloroform-d, 298 K) of G1 Cl Et 3 DCM Scheme S2 Synthesis of G2 Synthesis of G2: 1,4-butanediamine (0.44 g, 5 mmol) and triethylamine (1.52 g, 15 mmol) were added in dichloromethane (50 ml). Then hydrocinnamoyl chloride (2.53 g, 15 mmol) was dropped to the mixture in ice-bath in 10 minutes. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered and washed with dichloromethane. The filtrate was washed by brine and dried by a 2 S 4. The organic layer was evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 60/1, v/v) to afford G2 (1.28 g, 72.7 %), m.p C. 1 MR (300 Mz, chloroform-d, 298 K) δ (ppm): (m, 10, Ar), 5.78 (s, 2, ), 3.18 (d, J = 5.66 z, 4, C 2 ), 2.97 (t, J = 7.59 z, 4, C 2 ), 2.50 (t, J = 7.62 z 4, C 2 ), 1.35 (t, J = 6.24 z, 4, C 2 ). 13 C MR (75 Mz, chloroform-d, 298 K) δ (ppm): 172.4, 140.9, 128.5, 128.4, 126.2, 38.9, 38.5, 31.8, LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd S4
5 for [M + a] +, , found R-ESI-MS is: m/z calcd for [M + a] +, C a +, , found Fig. S3 1 MR spectrum (300 Mz, chloroform-d, 298 K) of G2 Fig. S4 13 C MR spectrum (75 Mz, chloroform-d, 298 K) of G2 S5
6 + 2 2 Et 3 DCM Scheme S3 Synthetic route to G3 Synthesis of G3: 1,4-butanediamine (0.44 g, 5 mmol) and triethylamine (1.01 g, 10 mmol) were added in dichloromethane (50 ml). Then di-tert-butyl dicarbonate (2.18 g, 10 mmol) was dropped to the mixture in ice-bath in 10 minutes. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered and washed with dichloromethane. The filtrate was washed by brine and dried by a 2 S 4. The organic layer was evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 80/1, v/v) to afford G3 (1.34 g, 92.9 %), m.p C. 1 MR (300 Mz, chloroform-d, 298 K) δ (ppm): 4.53 (s, 2, ), 3.12 (s, 4, C 2 ), 1.50 (m, 4, C 2 ), 1.44 (s, 18, C 3 ). 13 C MR (75 Mz, chloroform-d, 298 K) δ (ppm): 156.0, 79.2, 40.3, 28.4, LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd for [M + a] +, , found R-ESI-MS is: m/z calcd for [M + a] +, C a +, , found Fig. S5 1 MR spectrum (300 Mz, chloroform-d, 298 K) of G3 S6
7 Fig. S6 13 C MR spectrum (75 Mz, chloroform-d, 298 K) of G3 Cl Et 3 DCM Scheme S4. Synthetic route to G4 Synthesis of G4: 1,4-butanediamine (0.44 g, 5 mmol) and triethylamine (1.52 g, 15 mmol) were added in dichloromethane (50 ml). Then butyryl chloride (1.60 g, 15 mmol) was dropped to the mixture in ice-bath in 10 minutes. The mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered and washed with dichloromethane. The filtrate was washed by brine and dried by a 2 S 4. The organic layer was evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 40/1, v/v) to afford G4 (0.46 g, 40.3 %), m.p C. 1 MR (300 Mz, chloroform-d, 298 K) δ (ppm): 5.85 (s, 2, ), 3.28 (d, J = 5.95 z, 4, C 2 ), 2.16 (t, J = 7.48 z, 4, C 2 ), (m, 4, C 2 ), (m, 4, C 2 ), 0.95 (t, 6, C 3 ). 13 C MR (75 Mz, chloroform-d, 298 K) δ (ppm): 173.4, 39.0, 38.6, 26.9, 19.2, LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd for [M + a] +, , found R-ESI-MS is: m/z calcd for [M + a] +, C a +, , found S7
8 Fig. S7 1 MR spectrum (300 Mz, chloroform-d, 298 K) of G4 Fig. S8 13 C MR spectrum (75 Mz, chloroform-d, 298 K) of G4 S8
9 C DCM Scheme S5. Synthetic route to G5 Synthesis of G4: 1,4-butanediamine (0.44 g, 5 mmol) were added in dichloromethane (50 ml). Then p-tolyl isocyanate (1.33 g, 10 mmol) was dropped to the mixture in ice-bath in 10 minutes. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtrated. The filter cake was washed by dichloromethane and water. Dry the cake to afford G5 (1.56 g, 88.0 %), m.p C. 1 MR (300 Mz, DMS-d 6, 298 K) δ (ppm): 8.26 (s, 2, ), 7.25 (d, J =8.47 z, 4, Ar), 7.00 (d, J =8.45 z, 4, Ar), 6.07 (t, J =5.62 z, 2, ), 3.07 (d, J =5.61 z, 4, C 2 ), (m, 4, C 2 ), 0.87 (t, J =7.29 z, 6, C 3 ). The clear 13 C MR spectrum of G5 could not be obtained, because it is not well soluble in DMS-d 6. LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd for [M + a] +, , found R- ESI-MS is: m/z calcd for [M + a] +, C a +, , found Fig. S9 1 MR spectrum (300 Mz, DMS-d 6, 298 K) of G5 S9
10 Cl Et 3 DCM 2 Scheme S6. Synthetic route to G7 P Synthesis of G7 p : 1,4-butanediamine (0.88 g, 10 mmol) and triethylamine (1.21 g, 12 mmol) were added in dichloromethane (170 ml). Then benzyl chloroformate (1.70 g, 10 mmol) was dropped to the mixture in ice-bath in 10 minutes. The mixture was stirred at room temperature for 12 hours. Some precipitates were observed from the reaction solution, and the resulting reaction mixture was extracted by water (20 ml), ethyl acetate (40 ml), and methanol (1 ml). The organic layer was evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 40/1, v/v) to afford G7 P (0.54 g, 24.3 %). 1 MR (400 Mz, DMS-d 6, 298 K) δ (ppm): 7.77 (s, 2, ), (m, 5, Ar), 5.01 (s, 2, C 2 ), (m, 2, C 2 ), (m, 2, C 2 ), (m, 4, C 2 ). Fig. S10 1 MR spectrum (400 Mz, DMS-d 6, 298 K) of G7 p S10
11 2 + dry DCM 2 Scheme S7. Synthetic route to Gs Synthesis of Gs: 2-itrobenzyl alcohol (0.766 g, 5 mmol) and 1,1-CarbonyldiiMidazole (1.62 g, 10 mmol) were added in dichloromethane (100 ml). The mixture was stirred at room temperature for 5 hours. The reaction mixture was washed by brine and dried by a 2 S 4. The organic layer was evaporated under vacuum to afford Gs (1.13 g, 91.8 %). 1 MR (300 Mz, DMS-d 6, 298 K) δ (ppm): 8.36 (s, 1, C), 8.19 (d, J = 8.12 z, 1, Ar), (m, 2, C), (m, 2, Ar), 7.12 (s, 1, Ar), 5.79 (s, 2, C 2 ). Fig. S11 1 MR spectrum (400 Mz, DMS-d 6, 298 K) of Gs DCM 2 Scheme S8. Synthetic route to G6 Synthesis of G6: 1,4-butanediamine (0.088 g, 1 mmol ) was added in dichloromethane (30 ml). Then Gs (0.49 g, 2 mmol) was dropped to the mixture. The mixture was stirred at room S11
12 temperature for 12 hours. The reaction mixture was washed by brine and dried by a 2 S 4. The organic layer was evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 60/1, v/v) to afford G6 (0.21 g, 47.0%), m.p C. 1 MR (300 Mz, chloroform-d, 298 K) δ (ppm): 8.08 (d, J =8.10 z, 2, Ar), (m, 4, Ar), 7.48 (t, J =7.54 z, 2, Ar), 5.51 (s, 4, C 2 ), 4.94 (s, 2, ), 3.23(s, 4, C 2 ), 1.58 (s, 4, C 2, overlapped with the solvent peak of water). 13 C MR (75 Mz, DMS-d 6, 298 K) δ (ppm): 156.1, 134.5, 129.4, 125.2, 62.3, LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd for [M + a] +, , found R-ESI-MS is: m/z calcd for [M + a] +, C a +, , found Fig. S12 1 MR spectrum (300 Mz, chloroform-d, 298 K) of G6 S12
13 Fig. S13 13 C MR spectrum (75 Mz, DMS-d 6, 298 K) of G Scheme S9. Synthetic route to G7 Synthesis of G7: G7 p (0.20g, 0.89 mmol ) and Gs (0.22 g, 0.89 mmol) were added in DMS (20 ml). The mixture was stirred at room temperature for 12 hours. The reaction mixture was washed by brine and extracted by ethyl acetate. The organic layer was dried by a 2 S 4 and evaporated under vacuum, and the residue was further purified by flash column chromatography on silica gel (dichloromethane/methanol = 40/1, v/v) to afford G7 (0.20 g, 55.9 %). m.p C. 1 MR (300 Mz, chloroform-d, 298 K) δ (ppm): 8.09 (d, J =8.06 z, 1, Ar), (m, 2, Ar), 7.47 (t, J =7.56 z, 1, Ar), (m, 5, Ar), 5.51 (s, 2, C 2 ), 5.10 (s, 2, C 2 ), 3.22 (s, 4, C 2 ), 1.56 (s, 4, C 2, overlapped with the solvent peak of water). 13 C MR (75 Mz, chloroform-d, 298 K) δ (ppm): 156.5, 155.9, 133.7, 128.5, 128.1, 125.0, 667, 63.2, 40.7, 40.6, LR-ESI-MS is: m/z calcd for [M + ] +, , found ; calcd for [M + a] +, S13
14 424.14, found R-ESI-MS is: m/z calcd for [M + a] +, C a +, , found Fig. S14 1 MR spectrum (300 Mz, chloroform-d, 298 K) of G7 Fig. S15 13 C MR spectrum (75 Mz, chloroform-d, 298 K) of G7 S14
15 3. Investigation of the interactions between EtP[5]A and Guest by 1 MR Fig. S16 1 MR spectra (300 Mz, CDCl 3, 298 K): (a) EtP[5]A (2.5 mm); (b) equimolar mixture of G1(2.5 mm) and EtP[5]A (2.5 mm); (c) G1 (2.5 mm) ; (d) 0.2 ml methanol-d 4 was added into the MR tube with the mixture of G1 (2.5 mm) and EtP[5]A (2.5 mm) in 0.5 ml chloroform-d. The association constant K a, G1 EtP[5]A value calculated from integrations of complexed and uncomplexed peaks of 1 of EtP[5]A is [(2.09/3.63) ]/[(1 2.09/3.63) ] 2 = 1279 M 1. The association constant K a, G1 EtP[5]A value calculated from integrations of complexed and uncomplexed peaks of b of G1 is [(1.35/2.35) ]/[(1 1.35/2.35) ] 2 = 1269 M 1. Therefore, K a, G1 EtP[5]A = ( )/2 = (1274 ± 5) M 1 S15
16 Fig. S17 1 MR spectra (300 Mz, CDCl 3, 298 K): (a) EtP[5]A (2.5 mm); (b) equimolar mixture of G2(2.5 mm) and EtP[5]A (2.5 mm); (c) G2 (2.5 mm) The association constant K a, G2 EtP[5]A value calculated from integrations of complexed and uncomplexed peaks of 1 of EtP[5]A is [(0.16/1.16) ]/[(1 0.16/1.16) ] 2 = 74 M 1. The association constant K a, G2 EtP[5]A value calculated from integrations of complexed and uncomplexed peaks of c of G2 is [(0.08/0.61) ]/[(1 0.08/0.61) ] 2 = 69 M 1. Therefore, K a, G2 EtP[5]A = ( )/2 = (71.5± 2.5) M 1 Fig. S18 1 MR spectra (300 Mz, CDCl 3, 298 K): (a) EtP[5]A (2.5 mm); (b) equimolar mixture of G3(2.5 mm) and EtP[5]A (2.5 mm); (c) G3 (2.5 mm) S16
17 Fig. S19 1 MR spectra (300 Mz, CDCl 3, 298 K): (a) EtP[5]A (2.5 mm); (b) equimolar mixture of G4(2.5 mm) and EtP[5]A (2.5 mm); (c) G4 (2.5 mm) Fig. S20 1 MR spectra (300 Mz, CDCl 3, 298 K): (a) EtP[5]A (2.5 mm); (b) equimolar mixture of G6(2.5 mm) and EtP[5]A (2.5 mm); (c) G6 (2.5 mm) S17
18 Fig. S21 1 MR spectra (300 Mz, CDCl 3, 298 K) of (a) EtP[5]A (2.5 mm) ; (b) equimolar mixture of G7(2.5 mm) and EtP[5]A (2.5 mm); (c) G7 (2.5 mm). The association constant K a, G7 EtP[5]A value calculated from integrations of complexed and uncomplexed peaks of 1 of EtP[5]A is [(1.05/2.05) ]/[(1 1.05/2.05) ] 2 = 861 M 1. The association constant K a, G7 EtP[5]A value calculated from integrations of complexed and uncomplexed peaks of b of G7 is [(0.49/0.96) ]/[(1 0.49/0.96) ] 2 = 851 M 1. Therefore, K a, G7 EtP[5]A = ( )/2 = (856 ± 5) M 1 4. Partial 2D SEY MR spectra of G1 EtP[5]A Fig. S22 2D SEY analysis of equimolar mixture G1 EtP[5]A in CDCl 3 (20 mm, 400 Mz, 298 K) S18
19 5. Study of the photocleavage G7 EtP[5]A via UV 365nm by 1 MR Fig. S23 1 MR spectra (300 Mz, CDCl 3, 298 K) of (a) G7 EtP[5]A (1 : 1, 2.5mM) in the absence (b) G7 EtP[5]A (1 : 1, 2.5mM)after UV 365 nm. 6. Reference S1. D. R. Cao, Y.. Kou, J. Q. Liang, Z. Z. Chen, L. Y. Wang and. Meier, Angew. Chem. Int. Ed., 2009, 48, S19
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